3,6-Bis(4-Biphenylyl)-2,5-Dihydropyrrolo[3,4-C]Pyrrole-1,4-Dione
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HS Code |
951630 |
| Chemical Formula | C34H22N2O2 |
| Molecular Weight | 486.55 g/mol |
| Appearance | Typically a solid, color may vary based on purity |
| Melting Point | Data may vary, needs experimental determination |
| Solubility In Water | Low solubility in water, likely hydrophobic |
| Solubility In Organic Solvents | Soluble in some organic solvents like dichloromethane, chloroform |
| Density | Data may vary, needs experimental determination |
| Stability | Stable under normal conditions, but may react with strong oxidizing or reducing agents |
| Uv Vis Absorption | Absorbs in certain UV - Vis regions characteristic of its conjugated structure |
As an accredited 3,6-Bis(4-Biphenylyl)-2,5-Dihydropyrrolo[3,4-C]Pyrrole-1,4-Dione factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 3,6 - Bis(4 - Biphenylyl)-2,5 - Dihydropyrrolo[3,4 - c]Pyrrole - 1,4 - Dione in sealed chemical - grade packaging. |
| Shipping | The chemical 3,6 - Bis(4 - Biphenylyl)-2,5 - Dihydropyrrolo[3,4 - c]Pyrrole - 1,4 - Dione is shipped in well - sealed containers. Special care is taken to prevent exposure, following safety protocols due to its chemical nature. |
| Storage | Store "3,6 - Bis(4 - Biphenylyl)-2,5 - Dihydropyrrolo[3,4 - c]Pyrrole - 1,4 - Dione" in a cool, dry place away from direct sunlight. Keep it in a tightly - sealed container to prevent exposure to moisture and air, which could potentially lead to chemical degradation. Store it separately from incompatible substances to avoid any unwanted reactions. |
Injection molding of polypropylene thin-wall packaging components incorporating 3,6-Bis(4-Biphenylyl)-2,5-Dihydropyrrolo[3,4-C]Pyrrole-1,4-Dione as a mid-shade red pigment requires precise control over shear history to prevent visible flow lines. Predispersion is carried out on a co-rotating twin-screw extruder with an L/D ratio of 40:1 at a melt temperature of 220°C to 240°C, using a single-pigment concentrate (SPC) at 40 wt% loading in a low-melt-flow homopolymer carrier resin. Letdown ratios typically target a final pigment concentration of 0.08% to 0.25% by weight, depending on part thickness. The molecule’s thermal stability ceiling—verified by thermogravimetric analysis under nitrogen at 10°C/min per ASTM E2550-21—exceeds 350°C with less than 1.5% mass loss, allowing coexistence with engineering thermoplastics such as polyamide 6 and PBT processed up to 280°C. However, the pigment exhibits a discoloration threshold when held at 300°C for residence times beyond 12 minutes, a critical boundary in hot-runner systems with dead spots. In polyolefin caps and closures, the migration fastness under EN 1186-1:2002 simulants (3% acetic acid, 10% ethanol, rectified olive oil) at 40°C/10 days consistently delivers values below the 10 µg/dm² detection limit, confirming suitability for indirect food contact under EU 10/2011. Lightfastness in polypropylene injection-molded plaques tested per ISO 4892-2:2013 (xenon arc, Method A, 3000 kJ/m²) routinely achieves Blue Wool Scale 7–8 in full shade, though the 1/25 standard depth tint shows a pronounced two-step fading: initial chroma loss of ΔE*ab ≤ 2.5 after 1000 hours, accelerating sharply beyond 2000 hours when residual crystal size distribution skews toward fine fractions below 50 nm. Production-scale molding trials on 120‑ton hydraulic machines report that screw recovery times must be kept below 8 seconds to avoid surging caused by non-uniform solids conveying when the SPC pellet bulk density drops under 0.55 g/cm³. Incorporation of 0.03% calcium stearate as acid scavenger is mandatory when processing in the presence of residual Ziegler–Natta catalyst residues to prevent metal-chelated color drift toward an orange hue.Coil Coating Topcoats and the 0.20 mm Polyester Primer BoundaryContinuous coil coating lines applying polyester-melamine topcoats pigmented with 3,6-Bis(4-Biphenylyl)-2,5-Dihydropyrrolo[3,4-C]Pyrrole-1,4-Dione operate at peak metal temperatures (PMT) between 224°C and 232°C for dwell times of 40–55 seconds. The curing kinetics of the hexamethoxymethylmelamine (HMMM) crosslinker, catalyzed by blocked p-toluenesulfonic acid at 0.5% on total resin solids, compete with a pigment crystal ripening phenomenon that shifts the hue angle hab from 28° to 33° when the oven temperature overshoot exceeds +6°C. A typical millbase formulation is predispersed to Hegman gauge fineness 7+ (< 5 µm) on a horizontal bead mill charged with 0.8–1.0 mm yttria-stabilized zirconia beads at a peripheral speed of 12 m/s, using a pigment-to-binder ratio of 0.65:1 and a high-molecular-weight polyester dispersing resin with an acid value of 18–22 mg KOH/g. Letdown to a final pigment loading of 6–9% in dry film (typically 18–22 µm DFT) yields a vibrant mid-red that resists boiling water blush for 60 minutes under ASTM D870-15 without delamination when a 5 µm chrome-free polyester primer is present. Without the primer, edge creep from scribe reaches 4.2 mm after 1000 hours of neutral salt spray (ASTM B117-19), attributed to cathodic disbondment accelerated by the pigment’s slightly basic surface amine functionality. Overbake resistance tested at 250°C for double the standard dwell time reveals an early warning threshold: Δb* shifts positive by 1.2 units, perceptible as a yellowing drift in whites formulated alongside, making titanium dioxide grade substitution necessary to keep the overall ΔE*CMC(2:1) below 0.8. Full-scale production at line speeds of 120 m/min on 0.45 mm hot-dip galvanized steel demands that the coil exit temperature uniformity across the web width be maintained within ±3°C, achieved through segmented infrared pyrometer feedback controlling gas burner zone ratios.What Limits Ink Transfer in High-Speed Solvent-Based Gravure Packaging?Solvent-based gravure printing on surface-treated biaxially oriented polypropylene (BOPP) and polyethylene terephthalate (PET) films for snack packaging utilizes 3,6-Bis(4-Biphenylyl)-2,5-Dihydropyrrolo[3,4-C]Pyrrole-1,4-Dione in nitrocellulose-polyurethane binder systems at press speeds reaching 350 m/min. The pigment’s primary particle size, controlled during a salt-milling step followed by solvent kick-out, must stabilize at a median D50 of 85–110 nm—narrowly dispersing the size distribution tail below 30 nm because sub-visible fines preferentially absorb the slow-evaporating solvent components, shifting the ink’s solvent-release profile and causing retained solvent levels to exceed 10 mg/m² as determined by headspace gas chromatography per EN 13628-1:2002. The ink formulation grounds the pigment at 8–12 wt% in a master batch diluted with a letdown varnish to 2.0–3.5 wt% final concentration, with viscosity adjusted to 18–22 seconds (DIN 4 cup at 25°C) using a blend of n-propyl acetate and ethoxypropanol in volume ratios of 85:15. Print trials on a rotogravure press with 70 l/cm electromechanically engraved cylinders document that dot gain in midtones (40% screen) expands by 7% when the ink temperature drifts above 28°C, attributable to reduced tack and increased pigment flocculation in the cell before transfer. Lamination bond strength with a standard two-component solvent-free polyurethane adhesive, measured as T-peel according to ASTM F904-16, remains above 2.5 N/15mm provided that residual free amine values in the ink film are held below 2 meq/kg; the pigment’s intrinsic 4‑biphenyl substituents do not introduce amine-related interference, but certain ink-reducing varnishes containing nitrocellulose with high nitrogen content (>12.2% N) can generate free nitrite radicals under UV sterilization lamps, initiating yellowing that departs from the initial chromaticity by Δb* ≥ 2.0 within 72 hours of post-cure exposure. Therefore, a nitrite-scavenging additive at 0.15% on total ink weight is incorporated when the package is destined for UV-treated filling lines.
As a p-Channel Semiconductor in Solution-Processed OFETs: Gate Dielectric Selection Dictates the Mobility Plateau3,6-Bis(4-Biphenylyl)-2,5-Dihydropyrrolo[3,4-C]Pyrrole-1,4-Dione functions as a donor-type semiconductor in organic field-effect transistors (OFETs) when its lactam nitrogen atoms are alkylated with branched side chains—often 2‑octyldodecyl—to confer solubility for solution processing. A top-gate bottom-contact architecture on a 300 nm thermally oxidized silicon wafer substrate (SiO₂ capacitance density 11.5 nF/cm²) using a fluoropolymer dielectric layer (Cytop CTL‑809M, thickness 450 nm) deposited from a perfluoro solvent yields a hole mobility extracted from the saturation regime at VDS = −60 V of 0.18–0.35 cm²/V·s, with threshold voltages clustered around −8 to −12 V when measured under nitrogen atmosphere with <0.1 ppm O₂ and H₂O. The semiconductor film is blade-coated from a 5 mg/mL solution in anhydrous chlorobenzene with the substrate held at 60°C, producing a thin-film thickness of 28–35 nm as confirmed by atomic force microscopy profile scans. Critically, mobility collapses to below 0.01 cm²/V·s when a bare SiO₂ gate dielectric is used without a passivating self-assembled monolayer (SAM) of octadecyltrichlorosilane (OTS), because the hydroxyl groups on the oxide surface trap charge at the interface and induce a poorly ordered semiconductor morphology. Annealing the cast film at 180°C for 30 minutes under vacuum (~10⁻⁶ mbar) increases the average domain size from 45 nm to 120 nm as estimated from grazing-incidence X-ray diffraction peak width at qxy ≈ 0.35 Å⁻¹, leading to a 2.3‑fold improvement in mobility over as-cast devices. Operational stability under continuous bias stress (VGS = −40 V for 10⁴ seconds) results in a threshold voltage shift of +4.5 V for the fluoropolymer-based device, versus +18 V for the SAM-only gate dielectric, proving that the low-κ metal-free dielectric minimizes interface trap generation. Fabrication of short-channel transistors with channel length L = 10 µm on flexible polyethylene naphthalate (PEN) substrates coated with a parylene‑C dielectric (1.2 µm, Ci = 2.5 nF/cm²) demonstrates a mobility retention of 90% after 5000 bending cycles to a radius of 5 mm, a test performed under ISO 21925:2021 guidelines for flexible electronics.
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The diketopyrrolopyrrole (DPP) derivative 3,6-bis(4-biphenylyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, available under laboratory designation DPP-BP-98, functions as a high-performance organic pigment engineered for applications requiring exceptional thermal endurance, migration fastness, and chemical inertness. Its molecular architecture — a 1,4-diketo-pyrrolopyrrole core symmetrically substituted with biphenyl groups — provides an extended chromophoric system that shifts the absorption profile bathochromically relative to simpler DPP analogues, while the rigid biaryl terminals restrict molecular mobility even when the pigment is dispersed in semi-crystalline engineering thermoplastics at melt temperatures exceeding 300 °C. Analytical specifications for the as-synthesised presscake typically report a purity above 98 % (HPLC, area-%), a median primary particle size (d50) between 0.25 µm and 0.45 µm as determined by laser diffraction (ISO 13320:2020), and a specific surface area (BET) in the range of 25–40 m²/g (ISO 9277:2022). The pigment’s low oil absorption, a consequence of the compact crystal habit promoted by the biphenyl end groups, permits high loading levels in masterbatch formulations without an excessive viscosity penalty during let-down.
Migration-fastness evaluations following ISO 105-A05:1996 demonstrate that the biphenyl-terminated DPP chromophore resists diffusion even in plasticised PVC and low-viscosity polyurethane coating films where conventional diarylide or monoazo reds exhibit blooming within 72 h at 80 °C. The mechanism is steric rather than purely solubility-driven: the large, rotationally constrained biphenyl moieties create a kinetic barrier to molecular reorientation and inter-lamellar transport once the pigment crystallites are dispersed in the binder. In forced-extraction tests using cotton fabric contact and a 2 kg load at 70 °C, colour transfer values remain below CIELAB ΔE*ab 1.5 after 500 h, meeting the most stringent automotive interior trim requirements. This performance places the compound ahead of Pigment Red 254, where the dichloro-substituted DPP backbone, despite excellent overall fastness, occasionally yields ΔE* values of 2–3 under identical conditions due to trace amounts of soluble by-products generated during pigment conditioning.
Without intermediate conditioning agents, the pigment’s crystal lattice exhibits a melting endotherm onset at 394 °C (differential scanning calorimetry, ISO 11357-1:2023), and isothermal thermogravimetric analysis (ISO 11358-1:2022) records a 5 % mass loss only above 415 °C in air. Consequently, the compound can be processed in engineering thermoplastics — polybutylene terephthalate (PBT), polyamide 6,6, and polysulfone — at barrel set points up to 310 °C without colour fade or plate-out on the screw. In powdered form, the pigment possesses a tapping density of 0.25–0.35 g/cm³ and a flowability (Carr index) below 25, making it suitable for gravimetric dosing in continuous compounding lines. The tinting strength, measured in a lithographic varnish against a barium sulphate white reduction at 1:10 ratio (ISO 787-24:1985), is around 105–115 % relative to a high-grade dichloro-DPP standard, attributable to the narrower particle size distribution achieved via controlled attrition milling.The biphenyl substitution pattern generates a rigid, highly aromatic molecular scaffold that resists nucleophilic attack by amines and thiols under typical service conditions. Immersion tests in 2 % aqueous ammonia at 60 °C for 24 h produce a ΔE* shift of 0.8–1.2, measured on a drawdown film of medium-oil alkyd, whereas comparative samples based on Pigment Red 254 exhibit shifts up to 2.5 due to partial hydrolysis of the diketopyrrolone ring. This enhanced hydrolytic stability permits the incorporation of the pigment into two-component epoxy-amine protective coatings that must survive immersion in alkaline cleaning solutions, a domain where many high-chroma red organics fail. However, prolonged exposure to strong reducing agents — notably sodium dithionite in textile bleaching baths — leads to reversible reduction of the carbonyl groups, causing temporary loss of chroma. Reactivation by air oxidation is typically >95 % complete after 48 h at 23 °C, but full recovery in thick films (>100 µm dry film thickness) may require elevated temperature cycling to 80 °C.
Solvent resistance profiles, assessed via 24-hour immersion in xylene, butyl acetate, and methyl ethyl ketone per ISO 2812-2:2018, show ΔE* values below 0.5 and no visible bleed, a critical advantage over benzimidazolone-based reds that can partially dissolve in ketonic solvents during coil coating oven traversal. The biphenyl group’s electron-donating resonance contribution red-shifts the visible absorbance maximum to approximately 545 nm (in polystyrene matrix), yielding a bluish-red masstone with CIELAB coordinates that typically fall near L* 49, a* 56, b* 18 (D65/10° observer). This places the hue between Pigment Red 254 (more yellowish-red) and certain performance-limiting perylene reds, allowing formulators to achieve deep, transparent maroon shades without the brownish undertone that can accompany quinacridone blends. The hiding power, governed by a refractive index near 1.8 and controlled primary crystal growth, permits film thickness reductions of 15–20 % versus conventional opaque reds to reach full coverage, reducing vehicle cost per square metre in coil and powder applications.
When compounded into semi-crystalline polyamide using a co-rotating twin-screw extruder with an L/D ratio of 44:1 and a screw profile incorporating three kneading blocks, the pigment’s thermal and shear stability allows masterbatch production at 35 % loading by weight, provided that the melt temperature measured at the die does not exceed 305 °C and the residence time remains below 120 s. A critical processing window exists: if the compound temperature surpasses 315 °C for longer than 90 s, a partial crystal phase transition from the α-modification to a high-temperature β-phase occurs, accompanied by a tribological shift in the melt viscosity and a 3–5 nm hypsochromic shift in the reflectance maximum. This transition is detectable in-process via a 5–8 % increase in extrusion pressure and manifests as a cloudy, opaque appearance in the finished moulded article instead of the desired transparent jewel tone. Therefore, processors employing hot-runner injection moulding with gate temperatures above 300 °C must validate thermal profiles using a differential scanning calorimetry scan of extracted moulding purgings, per ISO 11357-3:2018, to verify that the α-polymorph fraction remains above 90 %. Pre-drying of the pigment powder at 110 °C for 4 h in a dehumidifying hopper dryer (dew point ≤-30 °C) is mandatory prior to let-down in moisture-sensitive matrices such as polycarbonate or thermoplastic polyurethane, as residual moisture levels above 0.15 % can catalyse ring-opening of the DPP core during processing, causing a yellowing of the shade and a loss of tintorial strength exceeding 20 %.
In solvent-borne industrial coating lines where pigment agglomerates resist high-speed disc dispersion, the use of a pre-dispersed chip or presscake with a d50 below 0.35 µm and a pigment content of 50 wt% in a plasticised nitrocellulose vehicle eliminates the flocculation-related shade drift that otherwise manifests as a ΔE* of 1.5–2.0 across batch intervals. Trials on a horizontal bead mill operating at 1200 rpm with 0.6–0.8 mm yttria-stabilised zirconia beads show that a let-down to 10 % pigmentation can be completed in a single pass when the chip’s pre-wetted surface energy is matched to the main binder’s Hansen solubility parameters δD at 17–18 MPa½. Without pre-dispersion, identical formulations require three passes, and the resulting ink-jet batch exhibits a gloss reduction of 8–12 GU (measured at 60° per ISO 2813:2014) due to undispersed micro-particles acting as surface texture defects. The compound is incompatible with driers based on cobalt octoate concentrations exceeding 0.05 % metal on binder solids, as cobalt-catalysed oxidative crosslinking can abstract electrons from the DPP ring system under UV exposure, resulting in a rapid fading measurable within 200 h of Xenon arc exposure (ISO 105-B02:2014, method 3).
Published data for lightfastness in full shade masstone, determined by Xenon-arc exposure behind window glass (method 3, ISO 105-B02), indicate a rating of 7–8 on the ISO grey scale after 1500 h, corresponding to a CIELAB ΔE* below 2.0 in an acrylic-urethane topcoat. Tinting strength retentions in white reductions (1:10 with TiO₂) under the same conditions exceed 95 %. These values are on par with or exceed those of Pigment Orange 73, a structurally related DPP, but the biphenyl variant achieves them without the need for UV absorber synergists. The difference arises from the inherently higher photostability of the biphenyl-chromophore conjugate, which quenches excited singlet states through rapid internal conversion rather than relying on radical scavenging. Consequently, formulations requiring 5–10 % lower UV absorber content are feasible, reducing plasticiser demand and improving film hardness.
The biphenyl DPP pigment does not contain any heavy metals regulated under EU RoHS Directive 2011/65/EU (Annex II) and complies with the purity specifications of Swiss Ordinance SR 817.023.21 for printing inks in food contact materials, with specific migration limits for primary aromatic amines below the detection limit of 0.01 mg/kg (simulant B, 40 °C, 10 days). It is listed on the Australian Inventory of Industrial Chemicals (AIIC) and pre-registered under REACH (EC) 1907/2006 with an annual tonnage band appropriate for specialty masterbatch. For use in toys, EN 71-3:2019+A1:2021 migration testing on pigmented polyolefin plaques yields results for all elements below Class 1 limits. Within powder coatings cured at 200 °C, overbake yellowing measured as the b* shift after 30 min at 230 °C is less than 0.8 units, substantially lower than that of benzimidazolone-based pigments that can drift 1.5–2.0 units under identical conditions.| Property | Test Method | 3,6-Bis(4-biphenylyl)-DPP | Pigment Red 254 | Pigment Orange 73 |
|---|---|---|---|---|
| Molecular weight (g/mol) | — | 456.5 | 357.2 | 400.4 |
| TGA onset, 5 % mass loss in air (°C) | ISO 11358-1 | 398 ± 5 | 375 ± 8 | 385 ± 6 |
| Full-shade lightfastness (Xenon, 1500 h) | ISO 105-B02 | 7–8 | 7–8 | 7 |
| Migration fastness, plasticised PVC 80 °C/500 h | ISO 105-A05 | ΔE* ≤ 1.5 | ΔE* 2.0–2.8 | ΔE* 1.8–2.5 |
| Resistance to 2 % NH₃ 24 h, ΔE* | ISO 2812-2 | 0.8–1.2 | 1.8–2.5 | 1.2–1.8 |
| Oil absorption (g/100 g) | ISO 787-5 | 35–42 | 45–55 | 40–48 |
Formulators accustomed to dichloro-DPP pigments must note that the shift in hydrophobicity profile, evidenced by a higher contact angle with water (95° vs. 78° for PR254 on a pressed pellet), can disrupt the adsorption equilibrium of conventional anionic dispersants. A switch from naphthalene sulfonate condensates to high-molecular-weight block copolymers with pigment-affinic groups terminated with biphenyl anchoring blocks — applied at 25–35 % active dispersant on pigment weight — restores Newtonian flow behaviour in high-solids millbases. Without this adjustment, suspension viscosities at shear rates below 1 s⁻¹ can remain above 5 Pa·s, causing pump cavitation in automotive basecoat circulation systems. No reactivity issues with isocyanates, epoxy hardeners, or melamine-formaldehyde crosslinkers have been observed under standard cure schedules up to 250 °C, although direct contact with raw polyisocyanate bulk at temperatures above 120 °C should be limited to under 2 h to prevent slow carbamate formation at the lactam nitrogen.
